


Principal's Pet (And Proud Of It)

by Imoshen



Series: SPN Kink Bingo 2019 [12]
Category: Supernatural
Genre: Anal Plugs, Anal Sex, Cock Warming, Consensual Relationship, Consent is Sexy, D/s relationship, High School AU, I'm Going To Hell For This, M/M, Panties, Spanking Mentioned, Teacher-Student Relationship, chastity play mentioned, or to be precise student-principal relationship
Language: English
Status: Completed
Published: 2019-01-26
Updated: 2019-01-26
Packaged: 2019-10-17 07:41:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,982
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17556158
Author URL: https://archiveofourown.org/users/Imoshen/pseuds/Imoshen
Summary: Dean Winchester is one of the bad boys. Until the door to Principal Chuck Shurley's office closes behind him.





	Principal's Pet (And Proud Of It)

**Author's Note:**

> No matter what it would be in reality, Dean is above 18 here, as I don’t do adult/minor. Their relationship is also fully consensual, even if I know the power dynamics are fucked up here. But Dean is 200 % on board.  
> I’m also not from the U.S., so I have no idea if you can graduate high school with full honors, I just took our system and applied it.
> 
> Cross-posted to tumblr @mrsimoshen.
> 
> Written for the SPN Kink Bingo, for the square High School AU on my card.

Dean Winchester is one of the bad boys of his school. He always wears his leather jacket, he smokes on school grounds, he flirts with all the girls (and some of the teachers) and he’s always up for helping with pranks.

But that’s during normal class times.

After hours…

 

Dean slowly walks down the empty school corridor towards the last door on the right.

The sign next to the door says, _Principal Shurley_ , in neat black letters, and Dean takes a deep breath before knocking on the door.

“Come in,” a warm voice invites him, and Dean pushes the handle down with another deep breath and walks into the room.

Principal Charles Shurley is still at his desk, apparently busy with some paperwork or other, and he looks up with a surprised expression on his face at seeing Dean before glancing at the clock. “Oh, I forgot the time,” he murmurs. “Hello, Dean.”

“Hello, sir.”

Dean closes the door and turns the lock before slowly walking up to the desk. He sets his backpack down in one of the chairs, and then, after a nod from the principal, rounds the wooden piece of furniture to stand beside Chuck.

“Any discomfort?” Chuck asks him, turning his chair so he can face Dean, who shakes his head.

“No, sir.”

“Good, good,” Chuck hums. “Show me, baby.”

Dean slowly undoes his belt and opens his jeans, pushing them down his thighs. Beneath them, he’s wearing a pair of pretty silk panties, pale lilac today with little white bows sewn on in a row down the front. He put them on this morning, in this very room, because the panties are always Chuck’s choice. Sometimes, he likes them, and this particular pair feels nice enough he thinks he might enjoy wearing them again.

Very pretty, baby,” Chuck murmurs, reaching out to run his fingertips along the waistband. “I still have a little work to do, so you will have to wait a little, but I think we can manage to make that good for you, hm? Undress – keep the panties on, I really like how they look on you – and then come back here.”

“Yes, sir.” Dean pulls his pants up far enough that he can walk over to the small couch Chuck has in his office. He undresses, carefully folding each article of clothing (he learned the hard way that Chuck doesn’t accept excuses for him not folding his clothes. He’d been locked into his cage for a week straight without relief and hiding that from Sam and Bobby and Ellen had been more than tricky. He’s been neatly folding his clothes ever since, even at home.) until he’s naked except for the panties. When he returns to where Chuck is waiting, he’s already breathing a little faster.

“So pretty for me, and so well behaved,” Chuck praises him with a gentle smile. “Come here, Dean, between my legs. Kneel down, baby.”

Dean smiles as he complies, sinking to his knees in his usual spot beneath Chuck’s desk. There’s a comfortable pillow on the floor already to cushion his knees, and Dean carefully arranges himself – legs spread, his ass on his heels, hands on his thighs, just as Chuck prefers him. The principal smiles at him. “Perfect, baby,” he praises, and Dean flushes with pride. Chuck laughs quietly.

“Now, let’s see,” the older man carefully slides his chair closer until he’s got Dean between his legs, and Dean digs his fingertips in to keep himself from reaching for his lover. “Very good, Dean, but you can go ahead and get my cock out.”

Dean purrs as he reaches to undo his lover’s pants and carefully draw the already hardening cock out of his underwear. Chuck hums at his touch and runs one hand through Dean’s hair. “Now, baby, this is what we’ll do: you take my cock into your mouth and keep it nice and warm, and I’ll work my way through the last of these pesky reports, and when I’m done, I’m going to bend you over my desk and fuck you, hm? Do you like that idea?”

Dean nods quickly. “Yes, sir!”

“Then get to it,” Chuck tells him with another low laugh, and Dean doesn’t need to be told twice. Permission given, he leans forward for a quick lick over warm flesh before taking Chuck’s cock into his mouth, letting it rest gently on his tongue and between his lips. He sighs happily as his lover cups the back of his head in one gentle hand as he goes back to work.

The position he’s in, the warm flesh in his mouth, the hand at his head, the fact that he was up at five this morning to be here early enough he could see Chuck before classes started, all of this combined has his eyes drift shut a few minutes in, and his world shrinks down to the touches, the little noises Chuck makes when Dean lightly sucks on him every now and then, the stroking fingers in his hair.

Dean blinks his eyes open when Chuck gently taps his cheek, making a questioning sound as he looks up.

“I’m done,” Chuck murmurs. “Now, baby, get me nice and hard so I can fuck you, hmm?”

Dean sets to work immediately and with enthusiasm, slowly moving his mouth up and down on Chuck’s cock, licking and sucking and purring as he feels him harden and swell in his mouth. He loves doing this, could do it for hours. Sometimes, Chuck indulges him, but today, he pulls him off gently after a couple of minutes. Dean whines, and Chuck laughs softly.

“I’ll let you suck me tomorrow,” he promises. “For now, up with you. On the desk, on your belly, baby. Let me see your pretty hole.”

Dean shivers as he slowly stands, Chuck’s hands on him providing stability. He gasps as he lays down on his belly on the cool surface of the desk, shivering a little. Chuck hums behind him.

“Gorgeous, baby,” he praises, and Dean flushes again and wriggles his ass a little. Chuck laughs and gives him a gentle slap to one silk-covered cheek. “Hold still, baby.”

Dean yelps, then moans as Chuck starts kneading his ass, slowly pulling the waistband of the panties down until it sits just beneath his cheeks. Chuck uses one hand to pull him open, and then Dean moans when his lover pulls on the plug he’d put in that morning.

“Sensitive, are we, baby?” Chuck gently pulls the toy out halfway and watches as it slides back in, accompanied by Dean’s moans. “How did this one feel inside you today, baby?”

“Felt good,” Dean breathes, whimpering as Chuck tugs the toy back out and lets it slide in again. “Reminded me of you every time I sat down, sir.”

The principal chuckles. “Good. Let’s see how stretched you are, baby.” He pulls the plug out slowly, letting Dean feel it sliding out, and sets it aside once it’s free of Dean’s hole. Dean whimpers as his hole twitches, feeling strange after being full the whole day. “Sir,” he mewls.

“Just a minute, baby.” Chuck reaches for his desk drawer and pulls a bottle of lube out, slicking up his fingers. “Need to make sure you’re nice and wet for me.”

Three fingers slide in easily, and Dean moans as Chuck slowly fucks him with them. “Yeah, you’re ready,” his lover decides, and then the fabric of Chuck’s pants is rubbing against the backs of Dean’s legs as Chuck pushes his cock into his hole. Dean groans and clenches down hungrily, fighting to keep from pushing back.

“Greedy little thing,” Chuck moans, rocking his hips until he’s in as far as he can go. “Fuck, you feel good around my cock, baby. Ready to get fucked?”

“Yes,” Dean moans, “yes, sir, please fuck me, need it so bad.”

“So polite,” Chuck praises, settling both hands on Dean’s hips. He sets a hard rhythm, and Dean can only cling to the desk and moan and beg for more breathlessly. He feels so damn good, his own cock hard in his panties, still rubbing against the silk covering him, and Chuck’s thick cock inside him rubs over his prostate every other thrust. He’s rapidly approaching the edge of what he can take, but he knows better than to come without permission, so he keeps moaning and begging for it.

“Want to come, baby?” Cuck asks, his voice now rougher as he pants. “Want to ruin those pretty panties for me?”

“Yes!” Dean mewls, trying to look over his shoulder at Chuck. “Please, sir, please may I come?”

“On my command, baby,” Chuck orders gently, picking up his pace. Dean wails as his prostate is nailed again and again, writhing on the desk where he isn’t pinned by Chuck’s hands on his hips. Chuck moans above him. “So desperate for me, baby, and so pretty with it.”

“Please, sir!” Dean’s close to sobbing with it, his orgasm so damn close he’s not sure how he’s holding back anymore. “Please!”

Chuck’s hands on his hips tighten. “Come for me, Dean.”

Dean screams as he does, writhing in his lover’s hold as he comes inside the panties, staining the silk with his release. His hole clenches down hard on the cock still fucking him, and distantly, he can hear Chuck groan. Hot wetness fills him, and he moans at the added sensation, panting.

“So good for me, Dean,” Chuck murmurs, running gentle hands over his sides now, stroking his back, his hair. “Such a pretty boy for me, coming so beautifully.”

Dean smiles, exhausted. He mewls protest as Chuck pulls out of him, and his lover chuckles and drops a kiss to his back. “Want to have the plug back, baby?”

“Please,” Dean slurs, and then groans as Chuck gently slides the toy back in. He’s tugged backwards after, and follows the gentle direction, boneless as he is guided into his lover’s lap. He snuggles into Chuck, resting his head beneath his lover’s chin, and sighs as strong arms envelop him.

In a moment, he’s going to get cleaned up by gentle hands, and then Chuck will help him get dressed, and drive him home – or almost home, since it wouldn’t do for Bobby or Ellen or even Sam or little Jo to spot his principal driving Dean home.

Chuck will kiss him, and tell him he loves him, and Dean will smile and nod and say the words back, and he’ll go to bed tonight still feeling his lover’s touch.

Tomorrow morning, he’ll be back here, before anyone else is at the school, and let Chuck’s knowing hands ground him for another day of classes.

 

Dean’s still one of the bad boys of the school, wearing his leather jacket and smoking on school grounds and flirting with the girls (and some of the boys). But since Chuck looked at him over his reading glasses, told him “if you really want me to stop – use the word _chapel_ , Dean,” and then proceeded to bend him over his lap and spank his bare ass until Dean, confused and babbling and sobbing, came all over his jeans, he’s become a little less wild, a little more manageable in classes.

He’s probably going to graduate with full honors next year, because Chuck doesn’t allow him to slack off in class (“you’re smart, Dean, I know you are, so concentrate on your schoolwork for now and if you do well, we’re going to play later.”) and then, he’ll go on to be the best goddamn vintage car restaurateur this state has ever seen.

And just maybe, when another year and a few months have passed, he’ll be able to go out with his gorgeous, caring ex-principal, and build a life with him.

Dean Winchester has plans, and the world should watch out.


End file.
